


Five Times Sam Was Topped

by Mayalaen



Category: Supernatural
Genre: 5 Times, Aggression, Begging, Bottom Sam, Consensual Sex, Crying, Desperation, Dirty Talk, Dubious Consent, F/M, Humiliation, Light Dom/sub, M/M, Manhandling, Object Insertion, Other, Painplay, Pegging, Rough Sex, Sounding, Strap-Ons, Tentacle Sex, Tentacles, Tickling, Top Abaddon, Top Castiel, Top Jody, Top Meg, Top Ruby
Language: English
Status: Completed
Published: 2015-07-30
Updated: 2015-11-11
Packaged: 2018-04-12 03:35:08
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 14,534
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4463927
Author URL: https://archiveofourown.org/users/Mayalaen/pseuds/Mayalaen
Summary: <blockquote class="userstuff">
              <p><a href="http://samanddeaninpanties.tumblr.com/post/122996462723/top-5-dicks-youd-like-to-see-in-sam">samanddeaninpanties</a> answered a "top five dicks you'd like to see in Sam," and it sounded like a to-do list.  I did it.  Hope you like it :)</p>
            </blockquote>





	1. Chapter 1

He didn't know she was a demon. At least not until he was on his back, legs in the air, and the hot blonde was ramming into him so hard, fucking him so good that he didn't even care anymore when he saw the smirk, the eyes turn black. Sam whimpers and begs when she pins his wrists to the bed, but he's not begging to be let loose.

"Please let me come," Sam says, eyes wide. "Please, Meg. Please!"

She's got him bent in half, and he knows he probably should've realized something was wrong when a chick not even close to his weight class shoved him back onto the bed and worked him open with his own bottle of lube, shoved her way into him with his own strap-on. She'd found it at the bottom of his duffel.

And as the demon pours itself into him, his orgasm making the whole thing so good it hurts, he begs her not to tell Dean. Because he's fucked up. He's gotten soft in his time away from his family, and he doesn't want to see the look of disappointment on Dean's face when he realizes his little brother not only begged a demon to fuck him, but that he'd do it all over again if he could.

*

It's Ruby's mouth that does it. She kisses him just a little too hard, sucks hickeys into his skin a little too close to the line of his clothing, and she licks his asshole just a little too long.

"Fuck me!" Sam growls, on his hands and knees, spread wide for her. The rough cement under his knees hurts, but he doesn't care. "Just fuck me already!"

Ruby chuckles. "So impatient," she says.

But Sam's had a good dose of blood, and he's not ready to be teased. He wants to get fucked. He spins around, the demon blood in him giving him strength and speed, which means he can catch her by surprise. She squeaks as he pounces, straddling her smaller body and lowering himself down over the strap-on.

"Oh, fuck yeah," he groans as he sinks down, eyes closing while he grabs a breast in each hand and squeezes.

He doesn't hesitate or let himself adjust to the fairly large dildo in his ass. He just starts fucking himself on her cock. He doesn't care if she gets off. He doesn't even want to ask her if she's having a good time. In fact the smirk on her face is annoying, so he leans down and bites her shoulder.

"Fuck!" she yells, back arching as he breaks the skin and sucks. "I already gave you some."

"Want more," Sam says, words muffled by her skin. Then he's hissing as she drags her nails down his back and over his sides.

She takes advantage of his momentary distraction and pushes him off. Before he can recover, she's on top of him, right hand grabbing a good chunk of his hair and holding his head down to the floor while she wrenches his left wrist up and behind his back.

"Yeah, fuck me," Sam says as she slams back into him.

She laughs, but she does as she's told. Sam tries to relax when she pushes his wrist up even more. If he makes a move, he'll dislocate his own shoulder. It's nothing he can't handle, but it would be an inconvenience, so he lets her do whatever she wants to him.

His hard cock drags over the concrete below him, but it only makes him harder. She's close, almost there. He knows because of the way she's panting. He's fucked her and been fucked by her enough times to know exactly what she sounds like when she's about to come.

"Fuck, Sam," Ruby hisses, and then she's coming, fucking him so hard he knows he's going to have some abrasions on the right side of his chin.

But then he's coming too, and the pain in his chin, the pain on the underside of his cock just doesn't matter at all when he's screaming his way through an orgasm, making a mess of the concrete and his stomach.

She pulls out of him and slaps his ass playfully. "Next time you get to top," she says.

By the time he gets to his knees and starts pulling his clothes back on, she's gone. All he has left is the emptiness in his ass, the uncomfortable stickiness of the lube drying on his ass cheeks, and a nice thrum of power running through his veins.

It's more than worth it.

*

He doesn't know her very well, and she's eying him up like he's some hardened criminal even though Bobby put in a good word for him. She's holding her nightstick, twirling it as she paces in front of the cell she's locked him in. He's standing in the middle of the cell, not really upset over what's happened. He'd been snooping, and it wasn't the first time he'd been in a jail cell.

"Bobby says I should let you go," Jody says.

She practically fondles the nightstick, hands running over it in a way that has Sam getting hard in his jeans.

"But," she drawls, "I'm tired of haulin' you two in here. Apparently my last warning meant nothin' to you."

She taps one of the bars of his cell with her nightstick once, twice, then wraps her left hand around it, caressing it. It's distracting, and Sam's not even sure he wants her to let him go at this point.

"Sam?" she says. "I'm talking to you."

Sam blushes, forcing himself to meet her glare. She noticed. She's been watching him and she saw him practically drooling over the fucking nightstick. He can see it in her eyes, the way she's smirking, and by the tilt of her head.

"Yes, ma'am," Sam says, but he has no idea what he's agreeing to.

"So you _do_ think I should keep you in here 'til Monday morning?" she asks, voice thick with sarcasm.

Sam mentally kicks himself. He must've been so focused on the stupid fucking nightstick that he didn't hear her question the first time.

"No, ma'am," he says, but he's not even convincing to his own ears. He's never been more grateful that Dean's passed out drunk at Bobby's, drooling on the couch.

Jody taps the shaft of the nightstick on the palm of her left hand, then wraps her fingers around it again. This time she's not even trying to disguise the fact that she's stroking it. He whimpers, blushing harder when he hears himself make such a needy noise.

"Maybe I'm going about this wrong," Jody says as she pulls out her keys and unlocks the cell door, the creaking of the hinges loud in the otherwise empty precinct. "Maybe punishment is what works best with your brother, but you need a reward system."

Sam's nearly shivering now that she's only about two feet away from him, still caressing that nightstick as if it's his cock. Or maybe hers.

"Yes, ma'am," he says politely, glancing back and forth between her too-intense gaze and her nightstick.

"I think a strip search is in order," she says, then taps his belly with the end of the nightstick.

He's pulling his clothes off before she's even done saying the words, and when he drops down onto the cot, making the springs squeak, she chuckles, obviously pleased by his enthusiasm. He makes quick work of getting his shoes and socks off, and scrambles back off the bed, stepping out of his jeans and underwear, standing naked before her, cock hard and leaking.

"Good boy," Jody says as she runs the nightstick over his cock, a gentle touch that has Sam whimpering, his cock twitching.

"Please," he says, and it sounds broken, desperate.

She likes it. He knows she likes it because she smiles with approval, the nightstick running under his balls.

"Which end are you beggin' for, sweetheart?" she asks, holding the nightstick up between them, letting him see the smoother, longer end of the stick, caressing it before she switches hands, holding the longer end with her left hand, letting him see the rippled handle with the mushroom head end cap.

"Fuck," he breathes. He wants it in him. He wants that mushroom head, wants those ripples fucking into him. He wants her to fuck him with it.

She points toward the cot. "On the bed, on your knees, legs spread, ass toward me."

He's already climbing on the cot, getting into position, but he hears her walking away, her boots receding. He panics a little, wonders if this was all a big joke and she's going to leave him like this, alone and horny while he pulls his clothes back on.

"Stay in position," Jody barks.

Sam chuckles, lowering his forehead to the bed and sticking his ass out like she'd asked. He doesn't care that he's leaking on her cot. For all he knows, he's not the first to spread for her like this. He hears her rummaging around in a desk drawer, then she's walking back into the cell.

"Beautiful," Jody says.

Sam flushes again, the compliment making his cock twitch again. His asshole clenches in anticipation as she runs her hand over his left ass cheek.

"You ever been filled up before, Winchester?" she asks.

He opens his mouth to answer, then gasps when he feels a dry finger circle his hole. "Y-yes, ma'am."

"Did you like it?" she asks, and really she doesn't need to. Sam couldn't be more obviously ecstatic about this.

"Yes, ma'am," he says, voice shaky with arousal.

She chuckles, a throaty sound that makes him shiver. "Do you think you can take me?" she asks, tapping his ass with the end of the nightstick.

"Yes, ma'am," he says, pushing his ass out even more. "Please!"

He makes some sort of noise that only comes out of dying animals when she pushes two lubed fingers into his hole, fucking in and out roughly. He's almost worried she'll back off because really, that noise was pretty ridiculous, but she must've realized it was a good dying-animal noise. She adds a third finger and taps his ass with the nightstick again.

"Please, please, please," he begs into the bed, wincing as he fights to stay in position.

She pulls her fingers out, and he almost comes just listening to her slick up the nightstick. It's wet and squelches, and he knows it's going in him, can't wait.

"Please, ma'am," he says. "Please fuck me."

"Oh, my, you're so polite," she says, rubbing the mushroom head over his hole.

He tries to push back, but she just moves with him, the stick running over and around and teasing and infuriating and frustrating and, "Oh, fuck, yes!" he hisses as she pushes the handle into him.

It feels better than he imagined it would. It fills him, the mushroom head and ridges making him squeak and almost fall out of position as she pushes it all the way in, the hilt resting against his crease.

She doesn't give him time to adjust.

"Fuck! Fuck!" he growls into the bed as she starts fucking him with the nightstick, the mushroom head dragging over his prostate in a way that has him babbling, begging, leaking on the bed.

It's all over so fast. Too fast. He's coming, blowing his load on the bed and his stomach, yelling nonsensical words without a care in the world that anyone else might hear him, his asshole clenching around the nightstick.

He hears her chuckle behind him. That throaty laugh again. It's still hot. She pulls the nightstick out slowly. It makes him gasp and squirm now that he's already come, his asshole used and sensitive.

"I'll let you out in the morning," she says, patting his ass and walking out of the cell.

By the time he flops over, naked and spent on the cot, she's locked the cell and is heading for the desk. She sits down and starts doing some paperwork. He doesn't notice right away, but soon he sees the nightstick on the cot next to him, still slick with the lube she'd used. He doesn't know if it's a promise for more of the same or just a reminder of what she did to him.

Either way, he knows he'll be getting in trouble fairly often whenever he's in town.

*

Abaddon has him by the throat, and all he can think is that he's relieved she's going after him and not Dean. He has no idea where Dean is, and he hopes his brother is okay.

"Ow, fuck," he whimpers as she slams him down on a table, his legs sprawled out over the wood, his hands grasping at her hand, trying to pull her off. He likes rough sex, but he also needs to breathe.

He's naked, just out of the shower, and he feels exposed on the wobbly motel room table, his torso the only thing really supported by it, his ass half hanging off the end of it.

"Aww, did you change your mind?" she asks, face hovering inches from his own.

His asshole clenches, his stomach almost sick, that feeling you get when you're falling and you don't know when you'll hit the bottom. But his cock is hard. He knows what's under her jeans. Or at least he knows what he's read about. He wants it. Wants it inside him.

"No," Sam says, voice strained.

"Ya look a little scared, Sammy-boy," she teases, grinning.

"Didn't expect to-," he says, then coughs as she loosens the hold on his neck. "Didn't expect to lose the ability to breathe."

She lets out a cackle that makes his skin crawl, tipping her head back. He hears the zipper of her jeans, but both her hands are still on him.

"Oh, fuck," he moans when he realizes every word he read about her is true. And he can't wait to see it.

The Queen of Hell has many responsibilities. One of which is to create more demons than just the ones sent down to her. A Knight of Hell is always equipped to step up to the plate, taking their place as queen.

Something's touching his leg, slithering over it. He flails, trying to sit up. If it's going to be inside him, he wants to see it. Prehensile. He remembers reading that. But he hadn't been able to find anything about the size of the thing.

"Shit," Sam says as his eyes widen.

The main tentacle is about as big around as his wrist, but the seven, maybe eight other tentacles are smaller, longer. They're all wet, all shiny black, and he thinks he sees suction cups. Nobody fucking said anything about suction cups.

"Oh, fuck, wait!" he says, scrambling a bit, panicking as he realizes the vulnerable position he's put himself into. He wanted it, but now that he has it, he's not so sure he wants it anymore. And the gleam in her eyes says she can kill him without even putting much effort into it.

"You're not the endgame," she says, smirking at him as the tentacles slither over his legs, tickling his balls and wrapping around his cock and poking at his hole. "You're just a good time while I'm up top."

It was meant to calm him down, and it works. She's not going to kill him. She's just going to fuck him with those things that are said to be addicting. He doesn't care if they are. He's already a slut for any woman ready to fuck him in the ass. Abaddon is just another, slightly more kinky version of that. He just wonders if she'll ruin him for other women. _Prehensile_ , his brain says over and over again.

She lets go of his neck finally, her hands smoothing down his sides as she nudges her way between his legs, grabbing his thighs and spreading him for her.

"Ah, fuck," he yelps as his back arches, the larger tentacle pushing its way into his hole. The other tentacles are rolling his balls and jerking him off, making the whole thing easier to take, but it's still big, and she's not giving him time to adjust.

It's tapered, and it's lubed with something he really doesn't want to think about, but it feels amazing, hurts like a motherfucker, but he's getting filled, the odd not-quite-firmness of the thing inside him different than anything he's ever felt before.

He's whimpering, loud and pathetic, but he can't stop himself, doesn't even try. His fingernails are digging into the splintered wood of the table, back arching as he tries to spread his legs more, spread himself open for her.

"What the fuck!?" he hisses as the thing in his ass gets bigger. No, it's not getting bigger. It's rippling. Waves of pleasure as the thing moves inside him, hitting his prostate just right.

He squeezes his eyes shut, clenching his teeth as some of the tentacles wrap around his balls, adding some pain to the mixture while the tentacles around his cock speed up, stroking him like no hand ever could.

"Hey!" he yelps, eyes opening as he tries to sit up, watching with no small amount of panic as one of the tentacles pushes its way into his slit.

He whimpers, the strange invasion only making the rest of what she's doing to him feel even better. His head thunks back down onto the table. He moans, not even embarrassed that Abaddon sees him like this, not when she's doing whatever the fuck it is she's doing to him.

"Oh, oh, oh," he cries out as yet another tentacle presses on his taint.

He feels himself floating, never having felt this much stimulation at once before. He realizes she really has ruined him for other women. He'll worry about it later.

"Such a slutty little boy," Abaddon teases, scratching her nails down his chest and stomach as she comes inside him.

He's not even thinking about the small paragraph he'd read. He's gone. He's coming harder than he ever remembers coming, possibly screaming his way through it, flailing on the table. He hears the table creak and doesn't care if the thing breaks apart beneath him.

It's over too soon, but he's still high on whatever endorphins all that stimulation released. It's not enough to override the sensation of her pulling out, the odd fullness remaining. And that's when he remembers that little paragraph he'd read.

"Thanks for the fuck, Sam," Abaddon says, smacking his leg before she heads for the door.

"Wait!" Sam says, trying to get his limbs to obey him. "How do I-?" he starts, but the door slams and he's left alone. "Fuck. Fuck, fuck, fuck. Fuck!" 

The table falls over as he's flailing desperately, tripping on his way to the bathroom and landing hard on his knees. It doesn't slow him down. He's crawling so fast there may as well have been a Hellhound after him.

Sam doesn't know if it would work in a human up top, but he's not taking any chances. He snags the gallon of holy water he'd left in the bathroom, a long tube lying beside it, and doesn't waste any time cleaning himself out, trying to forget about the word eggs. He's cleaning out come, nothing else. She came inside him. That's it. He'll be okay.

It's still worth it.

*

Sam thinks Cas is adorable. Especially when he looks so vulnerable. Sam doesn't know how a creature as old or as powerful as Cas is could look so fragile at times, but he does, and after he gets his grace back, he doesn't lose that lost look he had during his time as a human. Sam knows it's because Cas' wings are damaged, and Cas feels useless, scared, alone because now he's lost his friend and that person he had the profound bond with to the influence of the Mark of Cain, to Hell.

Sam really shouldn't have pushed. Shouldn't have teased. But he's just so angry. At the world, at his brother, and at the forces or powers that be who continually screw all of them over. And over and over.

He doesn't even see Cas move, but suddenly the creature is snarling in his face, holding him against the wall with powers that are more than just physical. Sam almost pisses himself. Because he can feel it. He can feel that sense of something larger than what his eyes are telling him he can see. It's never been directed at him before, and he's terrified. He doesn't even want to think about what this would feel like if Cas was at full power.

"Is this what you wanted?" Cas hisses in his face, giving him a little shake, which makes Sam's head smack back into the wall he's pinned against. His own fucking wall in his own fucking bedroom.

Sam can't make himself speak, and as Cas leans in closer, letting out a sound that can only be called a growl that rumbles through him, Sam finally loses the battle with his bladder. He pisses himself. Warmth spreading over his crotch and down his legs. It turns cold much too quickly, and the way Cas' lips twitch only adds to the humiliation.

"Staying out of your head is a courtesy," Cas says, voice low, "one I offered to you and your brother because of everything you'd done for the world. Pushing me the way you've done over the past few weeks?" says, then cocks his head to the side, "You no longer have the privilege of privacy."

Sam feels tears gather in the corners of his eyes. He's so scared that he can't even control the way his bottom lip is quivering. Cas is shorter than him, but he's never felt more overwhelmed, more surrounded by another individual. He doesn't know what to say, what to do. He's teased, he's pushed, he's needled, and this is what he's gotten. He deserves it, but that doesn't mean he's going to be able to handle it.

He tries to remind himself that Cas loves them, has fought by his side. But Sam, of all people, knows how far someone can go, how they can hurt someone they love. Especially when they've been pushed to their breaking point.

"You've manipulated," Cas says. "You've coerced and lied."

Tears run down his cheeks. He knows exactly what Cas is talking about. Charlie. He'd hidden it from Dean, caused yet another death. Cas blames him.

"No," Cas says, giving him another shake. "You're not paying attention. You're assuming. She made her own choices. We all hid it from Dean. You're no more to blame than the rest of us."

He can't stop the tears, and soon he's sobbing, heaving breaths that make his chest ache, his eyes burn, and he feels like a rag doll hanging from Cas' hands, his energy drained.

"You're still looking at life through the eyes of a victim," Cas says. "Stop."

"I d-don't know what you mean," Sam says, sniffling as he blinks the tears from his eyes.

"All of us are warriors," Cas says, "and so was Charlie. She didn't need to die the way she did, but she didn't regret her decisions. She died trying to save Dean, and she gave us a key that even Rowena couldn't give us. We're not victims. We're warriors. She should be honored as such."

But it's his fault. It's his fault The Darkness has taken over the world. His fault cities are dark and Dean is running Hell with the Mark burned into his arm yet again. It's his fault thousands of people have died. It's his fault that he and Cas can only fight hundreds of tiny wars instead of fixing the apocalypse he's started. Again.

"You really think Dean's down there torturing souls and earning black eyes?" Cas asks, lips twitching again.

Sam feels more tears run down his cheeks. "It's my fault."

Cas lets out a huff of laughter. "You know your brother better than that. You know _me_ better than that. The only one you don't know is yourself. You're not going to quit, and neither are we. We never have before."

"How do you know?" Sam asks, because Cas can't go to Hell in his condition. Fuck how well he thinks he knows Dean. Cas doesn't know what's going on down there.

"Crowley gave you that book," Cas says.

Sam looks over at the desk in the corner of his room. His stomach nearly rebels when he thinks about all the people who are enslaved, who can't have a home anymore, can't have a desk of their own while he's staying in the bunker, everything just as nice and clean as it was before The Darkness. It's a shock when he goes on a food run, seeing the devastation out there, and it's only by some miracle that millions or possibly billions of people aren't dead. Maybe they'd be better off if they were dead. Living life as a zombie isn't really living.

But yes, the desk. On top of it, open and waiting for him to finish it is the book Crowley has given him. He didn't think much of it at the time, and he still doesn't really know why it's so important.

"The binding on the book," Cas says.

Sam nearly rolls his eyes. Cas has him pinned against the wall. He _can't_ see the binding.

"You already saw it," Cas says. "You know where it's from."

And Sam does. At least now he does. Human hands didn't make that book. It's from Hell. And if he just finishes it, figures out what Dean was trying to tell him by using Crowley as his errand boy, maybe they can save the world.

"But you were too distracted," Cas says. "You were reading through that book like it was a fairy tale."

"I'm sorry," Sam whispers. He's failed again.

"You were distracted because you've been fighting The Darkness for three years now," Cas says. "Nonstop, only eating and sleeping to keep yourself fit for battle. You haven't smiled or laughed in all that time. You haven't pleasured yourself. You haven't accepted the touch of anyone in that time."

Sam can't look Cas in the eye anymore. It hurts. Because it's true. He's been focused on fixing everything he'd fucked up, cutting out everything he didn't deserve. He lets out a squeak as Cas leans in and kisses him. It's soft and gentle and everything he doesn't deserve. It's wrong and fucked up. But he melts against Cas all the same.

He doesn't want gentle, but he kind of does. And as Cas spreads him out on the bed, Sam cries. His brother was right. Sam Winchester cries during sex. Especially when Cas kisses every part of him like he's precious, fingers moving over his skin whisper soft, not leaving bruises or scratches behind.

And when Cas pushes finally pushes into him, after Sam is a begging, shivering mess, Cas' cock fills him up in a way he hadn't experienced since before he'd doomed the world. Sam lets him in, lets Cas take care of him, lets Cas whisper words of love and devotion against his skin. There's no aggression, no pain, no hurry to the end, and when he comes, Cas' cock moving in and out of him slow and steady, Sam cries out into Cas' mouth, arms wrapped around the smaller body, holding on for all he's worth.

When it's over, Cas kisses his cheek, his forehead, his neck, then his mouth again before giving him one last smile and walking out of the room, leaving Sam to his research. The book was never meant for Cas. Sam knows that now. Cas wasn't meant to figure this out, and Dean knew exactly what he was doing when he sent Sam the book.

Sam rolls out of bed and sits down at the desk, Cas' release leaking from his hole, but he doesn't care that he's possibly ruining the wood of the chair. There's an answer somewhere in the pages of this book, and he's going to find it. He's a warrior, not a victim. He's going to fight.


	2. Part 2

**Summary for the Chapter:**

> [Sandra's](https://archiveofourown.org/works/4463927/comments/38119871) request for my [Tumblr Ask Box Requests](http://mayalaen.tumblr.com/post/122749813129/ask-box-requests) ([on AO3](http://archiveofourown.org/works/4244124/chapters/9603369)). Sandra's Request: Wonderful fic, I love when big man like Sam bottoming, this is so hot, I'd like see him fucked by Dean and Charlie any chance for sequel?”
> 
> The first chapter of this fic was originally a sort-of request by [samanddeaninpanties](http://samanddeaninpanties.tumblr.com/). These vaguely follow canon, but not really, just like the first chapter.

**Notes for the Chapter:**

>  **Please Note:** If you’d like to avoid the Wincest, just skip parts 3 and 5, which are labeled as Sam/Lisa (with voyeur!Dean) and Sam/Dean. The rest of them don’t mention Sam/Dean other than Dean wanting to know what’s going on and Charlie talking about teasing Dean with details, which can totally be taken as horny!Dean wanting details about Charlie’s sex life, not necessarily about Sam.
> 
>  **Tags for This Chapter:** Sam/Jess, Sam/Pamela, Sam/Lisa with voyeur!Dean, Sam/Charlie, and Sam/Dean, pegging, manhandling, rough sex, biting, light spanking, strap-ons, dirty talk, light D/s, tickling, begging

**Part 1: Jess**

He needs a roommate, and when the amazingly hot girl with blonde hair and a beautiful smile shows up, ready to move in and able to help with the rent, he can't say no.

Jess is easy to live with. It isn't just because she's hot. She likes the same movies he likes, eats a lot of the same foods, and she doesn't hesitate to call him on his shit, which isn't always fun, but the part of him that misses home, that misses Dean and the close relationship he's had with his brother, that part is soothed just a bit by an elbow to his gut when she teases him for not getting a dirty joke she's told. And when she laughs and shoves him out of the kitchen because he's sweeping up broken glass without shoes on.

She catches him jerking off on the couch one night, and as he stammers and blushes, she just chuckles and plops down on the couch next to him, reaching into her panties and poking him with her toe when he just sits there and stares, mouth hanging open.

It's not love. At least not at first. It's friendship and someone who cares, and a little bit of the empty hole in his life is filled up. She's funny and charming and headstrong in a way Sam has never seen in a woman. Sam wonders what Dean would think of her, but he already knows. Dean would love her.

"You're into that?" she asks from behind him.

Sam would never have lived down the scream had Dean been around to see him nearly fall out of his chair. Sam almost snaps the hinge on his laptop as he slams the top down.

"No, I was just looking," Sam says, turning around to scowl at her.

It's too late. She knows him well. "You like it," she says, and he can't read the look on her face. She definitely isn't smiling, but she doesn't seem outright pissed either.

"No, I don't," Sam argues, but she's already backing out of his room. "Jess, wait!" he says as she disappears around the corner. "Shit."

She's been okay with so much. All those late nights she's listened to stories about his life, stories that have never thrown her, and this is it. He's gone too far with his strap-on fetish. He runs his hand over his face, stomach twisting because he really does like her. And if Dean had walked into the room and demanded to know, he would say he loves her.

"You're so cute when you're freaking out," Jess says from the doorway.

Sam sighs, opens his eyes, and forgets how to breathe. Because Jess -- his adorable, sexy, funny, awesome roommate -- is leaning against the doorway with a strap-on dangling from her left index finger.

"Oh, fuck," Sam whispers, eyes wide.

"Wanna?" she asks, waving the thing back and forth.

"Really?" he asks, voice cracking. She isn't the type to tease him _that_ badly, but there's a part of him that can't believe she's really offering.

Jess chuckles as she walks into the room, getting close enough that her knee brushes against his, then pushes her right hand down her pajama pants. Sam moans as she does something down there, and then she pulls her hand out and shows him her slick fingers.

"Does that answer your question?" she asks, and yes, that's a challenge.

"Uh-huh," Sam says, nodding.

"You should probably get your clothes off," she says, then sucks her fingers clean.

Sam comes close to falling on his face twice as he tears his clothes off, and by the time the last piece of clothing is tossed across the room, she's standing at the end of his bed, naked now that she's dropped the pajama pants and pulled the tank top off.

"Wanna watch me put it on?" she asks. Sam nods, movements almost spastic. "Get on your knees. On the bed, facing me."

Sam does as he's told, resting his ass on his heels and spreading his knees, knowing she likes having a full view of him. Sam trembles as she steps into the harness, one foot at a time, then slowly pulls the straps up her legs. She's beautiful. So fucking beautiful. Confident and sure of herself in a way that's almost painful because it reminds him of someone else.

"Do you want me to fuck you on your back or knees?" she asks as she tightens the straps.

"Whatever you want," Sam replies, and he means it. He'll do anything for her.

"Okay, then get on your back and spread for me," she says as she crawls onto the end of the bed.

Sam plants his feet on the bed and spreads wide, cock hard and leaking on his stomach. She crawls to him, then kneels between his legs before grabbing her cock and slapping it on his left inner thigh. Sam bites his lip because it's fucking hot how she holds it, like she uses it all the time, like it's real and not something she steps into.

"Gimme the lube from under your pillow," she says.

Sam chuckles, reaching under the pillow and grabbing his half-empty tube of lube, handing it to her and feeling a warmth inside because she knows exactly where it is.

"You ever done this before?" she asks.

"A few times," he says.

"Good," she says, nodding, "then I don't have to worry about wrecking your poor little hole."

Sam chuckles, but she just looks right back at him, left side of her mouth quirking up in a half smirk. "Oh, shit," he breathes, because she's fucking serious. He whimpers as she pushes a lubed finger inside him, so turned on that he's nearly vibrating with need.

"We'll get there," she says, adding a second finger.

"I'm good," Sam says, glancing down at where she's pushing into him.

"Okay," she says, smiling as she pulls her fingers out and slicks up her cock.

It's thicker than he normally sees on harnesses, and there's ridges on it, accentuated by the swirled purple and pink throughout the dildo. Sam holds his breath as she pushes in, forcing himself to take it. It burns, and he probably should've let her prep him more, but it feels amazing, and Jess isn't the type to spend a lot of time on foreplay anyway.

By the time she bottoms out, he remembers to breathe, letting out a loud moan as she puts her hands on his knees for leverage and starts fucking him. Her tits bounce a little as she moves, and he wants to touch. He reaches out and tweaks a nipple, making her hiss and lose her rhythm for a moment. She loves having her nipples played with, and if they were in a different position, he'd be sucking on them, nibbling, and mouthing around her breasts. Instead he cups her left breast and squeezes a little.

"Still think I'm gonna kick you out?" she asks.

"I didn't...," Sam says, then lets out a chuckle. "Okay, yeah, I did think that."

"Suck a dork," she says, shaking her head.

"Yeah, but that's why you love me," he says, then realizes what's just come out of his mouth and looks her in the eye, hoping she's okay with it. He knows she won't be mad, but he also doesn't know if she'll take the opportunity to say this isn't love, only fucking.

"Yeah, that's part of it," she says, as if she's thinking about it, then drapes herself over his chest and stomach, her skin so soft against his. "But I also think it has something to do with the way you look at me when I'm talking about art or showing you one of my paintings," she says as she trails kisses over his jawline. "And the way you leave a breakfast sandwich on my bedside table some mornings when I don't have an early class. And the way you never bitch at me about leaving wet towels on the bathroom floor."

Sam's chest feels tight. "I like watching you sleep," he says, then winces, because that sounded really stalker-y.

Jess chuckles. "You're adorable when you try to flirt. That's another thing I love about you."

Sam's face flushes. He's really terrible at flirting. He hopes when he gets older it'll get better. "And I don't mind the wet towels on the bathroom floor because you also leave your dirty panties behind."

"Oh, did you think that was an accident?" she asks, blinking innocently.

"No," he says, grinning as he runs his fingers through her hair.

"Good," she says, then kisses his chest. "I was hoping my seduction techniques weren't going to waste."

"They weren't," Sam says. "You've got me."

"You're all mine?" she asks, and it's more than just a flippant question.

"If you want me to be," he says, his chest nearly about to explode.

"Only if I'm all yours," she says, looking him in the eye.

The little black velvet box is at the bottom of his underwear drawer, and he already has his answer. He wonders if she'll squeal with delight when he presents her with the ring or if she'll punch him in the arm and tease him about how much money he's spent.

Either way is totally fine with him. He loves her.

**Part 2: Pam**

She misses seeing the blush on Sam's cheeks, the way he ducks his head, curling in on himself and somehow appearing smaller than her even though he's so much bigger.

"Please," Sam whines. "Pam, please!"

She may be blind, but she can still feel the heat of his body beneath hers, hear every whimper and gasp, taste the sweat on his chest as it heaves with his breaths, and smell just a hint of cologne and leather underneath the heavy odor of sex in the room.

"Oh, fuck, Pam," Sam gasps as she spreads him wider and goes in even deeper.

"You'd better not come before me," Pam says, smirking down at him.

Sam whimpers, then hisses as she doubles the speed of her thrusts, nearly bending him in two because she's stronger than she looks, which is part of what turns Sam on. He already came in under a minute after she got her cock inside him, so really he should be able to hold it, but everything about her is intense, and she loves that he almost can't handle her.

"I-I'm not gonna," he promises.

She can't see him, but she knows he's beautiful. Flat on his back in her bed, hair plastered to his forehead because he's been sweating like a pig even though she's the one doing most of the work. She's not even naked. She's got a black T-shirt on, snug-fitting, and her black lacy bra underneath that she knows he wants to see, but he's letting her call the shots. Her strap-on is the only thing she's got on from the waist down.

"Don't touch," Pam barks.

"I wasn't gonna!" Sam says, and she can hear the surprise in his voice.

"Yeah, you were," she says, fucking him harder.

"How do you know?" he asks, and then he realizes how insensitive that was and stammers a bit.

She doesn't mind. Really. In fact, she thinks it's funny that he's so careful about the loss of her sight. She's fine. She's learned to deal with it and wasn't lying when she said she still has more senses than most people anyway. But Sam's a sweetheart deep down, so even though he can get aggressive with sex, likes it rough, he'd never hurt her.

"You were grabbing the sheets," she says, distracting him and giving him a taste of what she's still got. "You were almost ripping my very expensive sheets, and then you let go, your hands started creepin' toward your dick."

He lets out a sheepish chuckle. "Sorry," he says.

"Am I gonna have'ta tie you down, boy?" she asks.

He fucking squirms beneath her, moaning as he mentally pictures what the threat means for him. "I'm sorry, ma'am," he says.

She files it away for later. She wants to come sometime tonight, and stopping now to get the ropes out would set her back.

"It's okay, Sam," she says, her hips slowing. "But I'm getting tired of holding your legs. Spread yourself for me."

The little gasp makes her clit twitch, her pussy clenching around the dildo inside her. He spreads himself, hands behind his knees, such a good boy for her.

"There we go," Pam says, voice low and gravely as she imagines exactly what he looks like. "Ready for me?"

"Yes, ma'am," he says, and she can hear him fighting for control over his own body. He wants to come. Wants to come so badly. But he's going to do his best to hold on until she comes.

She's not worried. Either way she's _going_ to come, and if he fucks up and comes before her, she's got a paddle in her bedside table with his name on it.

"You know what happens if you come first," she says as she puts her hands on his chest and lowers herself on top of him, his cock squished between their bodies, her shirt scratchy on his nipples. She licks his neck and nips at his jaw.

"I won't," he says.

"It was kinda fun last time," she says, chuckling against the skin of his neck as she fucks him, rolling against him in a way that won't get him off, but it feels great on her clit because of the way the harness and her own dildo are built. "Ridin' the back of your thigh while I turned your ass read with my paddle? Yeah, that was fun."

Sam lets out a chuckle. "Fuckin' hurt," he complains, but she can tell he's smiling.

"Yeah, but I had a good time," she says, hips moving faster as she wraps her arms around his upper chest, hands between him and the bed. "I came just rubbin' my pussy on your leg. Remember that?"

Sam hisses, and she can feel his body jerking beneath hers. He almost came, and she's impressed by the way he holds it together. He takes a few breaths to calm himself.

"Yes, ma'am," he says, voice strained.

"Have you thought about that while you're jerkin' off in the shower?" she asks, then kisses his chest while she grinds against him.

"Fuck, yeah," he says.

She chuckles. "Did you come hard for me?" she asks, like it was still her orgasm even though she was nowhere near him at the time.

"So fuckin' hard," he says, tiling his hips up so she can get even deeper inside him.

"Mmm, so tell me," she says, rolling her hips, almost there, "was it the thought of my pussy rubbin' all over your leg, wet and hot, or was it the way I was smacking your ass with my paddle and playin' with your hole that got you off?"

He shudders beneath her, a full-body thing as he whimpers, and it's so fucking hot, so erotic that it tips her over the edge and she comes, shoving her cock deep inside him and moaning, closing her eyes and panting against his chest.

Sam doesn't say anything, just waits while she comes down from her orgasm, body loose and sated on his. He's always patient with her, lets her set the pace.

Pam sits up, getting her knees back under her, and slides the harness to the side a bit so she can get the dildo out of herself. He watches, eyes wide, cock hard and dribbling onto his stomach.

"I'm gonna make you come," she says, then holds up the wet dildo. "Do you want me to fuck you with this or the strap-on while I play with your cock?"

She nearly laughs when he hesitates. It's a hard decision because the dildo was just inside her, and it turns him on, but Sam never comes harder than he does with a strap-on pounding into him.

"Too late," she says, smirking when he chuckles. "I get to decide now. Let go of your legs and suck on this while I fuck you," she says as she hands him the dildo.

"Oh, fuck," he says, and his hands shake as he takes the dildo from her.

"When you come, I wanna hear you moaning around that cock in your mouth, got it?' she asks.

He forgets she can't see him and nods instead of saying something, but she can hear his head moving on the pillow, can sense his movements, and she doesn't point it out. She doesn't want to make him feel bad, not when they're both having such a good time.

"Good boy," she says, then pushes her cock inside him again.

She can hear him breathing heavily through his nose, can hear the wet sounds of him sucking and licking her juices from the dildo, and even though she can't see him, she knows he's looking right at her. He may be enjoying himself, but he never loses that contact, that sense of being with another person in bed.

Pam grabs his cock and smacks it down on his stomach in the mess he's made, a wet sound that makes her clit twitch. She strokes him in time to her thrusts, focused on making him feel good, because she loves how hard he comes, and she wants to hear every bit of it, feel everything.

It doesn't take long. She knew it wouldn't. He's too excited, too turned on, and she loves that she does this to him. He whimpers and moans around the dildo in his mouth.

"You gonna come for me?' she asks, pushing his right leg out and up, hand behind his knee an lifting his ass off the bed just a bit so she can hopefully hit his prostate.

She changes the angle of her thrusts and he cries out, making her smirk. She may not hit his prostate every time, but she can damn well try. His cock jerks in her hand, and then he's letting out long moans around the dildo in his mouth, his back arching, his cock spilling onto her hand, dribbling instead of shooting because she's played with him too long.

Pam slows and finally comes to a stop, letting go of his cock and licking her hand clean. 

"Oh, that's so fuckin' hot," he slurs, reaching up and grabbing at her.

She chuckles as he pulls her down on top of him, her cock still inside him, the dildo forgotten on the bed. She kisses him, sharing the taste of his own release with him, and he holds her, the both of them as gentle as they ever get when it comes to sex.

"So fuckin' hot," he says against her lips, nips her bottom lip. He has one hand in her hair, just playing with it while the other hand caresses her back.

"You're not so bad yourself," she says, resting her head on his chest and settling down.

She stays inside him as he drifts off for a while. Later, when he's softly snoring, she wakes him up by starting all over again, chuckling when he moans himself awake.

**Part 3: Lisa**

Lisa laughs the first time she makes a pass at Sam and he nearly runs from the house. Dean's standing right there, right in the kitchen with them, and Sam's eyes are so wide he knows Dean's going to tease him for weeks, maybe the rest of his life.

Sam's plastered against the kitchen wall, his heart racing, but the two of them are standing there nudging each other, chuckling as if Sam is totally adorable for having freaked out.

"Dude, would you chill out? I'm okay with it," Dean finally says, holding his hands out at his sides.

"Huh?" Sam says, face screwing up in confusion. He wonders if he stepped into another dimension when he walked through the front door a few minutes ago.

"She's kinky," Dean says, grinning and winking at him.

"But...," Sam starts, but he really doesn't know how to finish his argument.

"Is it because we're brothers or because you think I'm gonna kick your ass for touchin' my girl?" Dean asks, shrugging.

"Uhm, well," Sam nearly squeaks.

"I've fucked girls in motels while you're in the next bed," Dean says. "Do you really think it's that much of a stretch I'd be okay with sharing?"

"But...," Sam says, and he still has no idea how to finish that.

"She's got a strap-on," Dean stage-whispers.

Sam's face gets so hot that he wonders if it's going to melt off. "H-how did you...?"

Dean grins. "Pam offered, thinking the kink runs in the family."

Sam's eyes get even wider. "So you, uhm...?"

"Pam and I fucked, yeah," Dean says. "But I need a lot of prep to take a cock, and we didn't feel like slowing down, so I took a pass on it."

"Oh," Sam says, mouth dry.

"Lisa has different sizes, so if you want somethin' big...," Dean says, as if he's talking about the weather.

"No, I..., but...," he says, then forgets how to speak entirely when Lisa walks up to him and cups his face with her hands.

"You can say no," she says. "I'll make sure he doesn't tease you about it. But I'm more than willing to do this if you're up for it."

Sam blinks at her for a moment, then looks back up at Dean. "Seriously? This isn't like a hidden camera thing? You're not gonna kill me after I say yes?"

"Ha! You didn't say 'if I say yes,'" Dean says, grinning and pointing at Sam, "you said 'when.'"

"Wanna see it?" Lisa asks, voice low and intimate, as if it's something she's sharing with only Sam even though Dean can hear her. "I'll let you pick out the one I fuck you with."

Sam opens his mouth, but his brain doesn't provide any words. He looks back and forth between Dean and Lisa, but neither of them are calling it off, so Sam decides to just stop freaking out. If they're okay with this, fuck it.

"Fuck, yeah," Sam says, his cock finally taking interest in the proceedings now that he knows Dean's not going to kill him.

"Awesome," Dean says, smiling.

"Come with me, big guy," Lisa says, taking him by the hand and leading him upstairs.

Sam feels lightheaded. It's not as if he and Dean were ever _that_ modest around one another. Hell, Sam's first blowjob was in the back seat of the Impala while Dean was making out with a girl in the front seat. Sam just never realized how okay Dean would be with sharing. He loved Lisa, didn't he? Sam didn't think he could have shared Jess.

Lisa turns him around when they get to the bedroom and starts unbuttoning his shirt. Sam tries to do the same for her, but is distracted when Dean walks into the room too. He feels his cheeks flush again and fumbles with Lisa's buttons. He can't remember ever feeling this nervous about sex, even his first time.

"Uhm, wait, you're...," Sam begins, and really, his brain is just having trouble keeping up.

Dean tosses his shirts on the floor and starts getting his jeans undone. "What?" he asks.

"You're staying?" Sam asks, having forgotten about getting Lisa out of her clothes and completely ignoring her as his jeans and boxers are tugged down.

"Well, yeah," Dean says, pulling a face, like it's Sam who's the idiot in this situation. "I've never watched her fuck a guy before. I gotta see this."

"But...," Sam says, then gasps as Lisa sucks his cock into her mouth. "Oh, fuck."

She's on her knees, hands on his hips, and she winks at him when he looks down. He doesn't know her as well as Dean does, but he has a feeling she did it to distract him. It's working.

"Relax, man," Dean says as he kicks his clothes to the side and flops down on the overstuffed chair opposite the bed. He grabs his dick and tugs it a little, mostly just handling it, not urgent to get hard.

"Just don't want you kicking my ass," Sam says, looking back and forth between Dean and Lisa.

"Nah," Dean says, shaking his head. "I'd rather watch it get fucked."

"Uhm, okay," Sam says.

"So how do you like it?" Dean asks. "Hard and fast or slow and sensual?"

Sam runs his fingers through Lisa's hair, moaning when she does a little something with her tongue. Her hair's soft and smooth in his hands. "H-hard," he says. "I like it when a woman just does what she wants. Even if I don't get to come."

"Fuck, yeah," Dean says.

"I like it when a woman treats the dildo like it's a real cock," he says, cradling her head as she bobs on his cock. "When she tells me how good it feels to fill me up with her big cock. I like when she slaps me with it. I like when she makes me take it."

"Heh, kinky," Dean says.

Lisa stands up, right hand on his cock, slowly stroking him, her hand getting wet with her own spit. She reaches up and grabs a chunk of his hair with her left hand, yanking his head down and to the side. Sam whimpers, eyes fluttering closed.

"You like it that Dean's in here?" she asks, and chuckles when his cock twitches in her hand. "That answers my question for me. Okay, I know exactly where I want you."

He's blushing, he's turned on, and he's almost scared to see the look on Dean's face. Because yeah, he's turned on that Dean's watching.

"Put your hands on his knees," she says, pulling him by his hair until he's standing in front of Dean.

"Oh, fuck," Sam whimpers, eyes wide as he puts his hands on Dean's thighs just above his knees. He looks Dean right in the eye and nearly calls the whole thing off. Dean's going to be watching him. He'll be right there the entire time. Sam has nowhere to hide, and the guy who knows all of his secrets except for this one will have a front-row seat to all of it.

"Wait 'til you feel it, Sammy," Dean says, grinning, still playing with his own cock. "She's a natural. Like she was born with it."

Sam flinches as Lisa gives his ass a good smack. "Down on your knees. You're way too tall for me to fuck standing up."

"Yes, ma'am," Sam says automatically, going to his knees.

"Fuck, that's hot," Dean says, grinning up at her. "Wish _I_ could get him to follow orders like that."

Lisa chuckles, letting go of her tight grip on his hair, then petting him. "He's a good boy when he wants to be, aren't you, Sam?"

"Yes, ma'am" Sam says as he spreads his knees, getting lower so she can get to him if she kneels behind him.

"Bet you always wanted to know what he looked like," Lisa says as she slaps her cock down on Sam's left shoulder, and yeah, she does use it like it's real. "He's pretty on his knees. Cheeks flushed, ears turning red while he makes a mess of the carpet."

Sam can't bring his eyes up. Can't meet Dean's eyes. He knows that means he's looking directly at Dean's cock, already hard and thick in Dean's hand, but he can't look Dean in the eye.

And then he really thinks about what Lisa just said. She's spent more time with Dean than other women, has lived with him for months, waking up in the morning to his obnoxious throat-clearing thing he does every fucking morning and going to bed every night with his cold feet touching her. And she's the one who set this up. She's the one who told Sam to get to his knees, to put his hands on Dean, and she's the one including the two of them in her dirty talk.

"How about you thank Dean and I for the privilege of getting this," she says as she smacks his shoulder again with her dick. "Because he usually doesn't share, and neither do I. This cock right here?" she says as she thrusts against his shoulder, the dildo dragging over his skin. "This has only been used on his ass. Nobody else's."

Sam almost comes right then and there. He squeezes the base of his cock as his breathing stutters and his eyes flutter closed. He can hear Dean chuckling, but he doesn't care. He finally gets it and it's fucking hot. He doesn't know if Dean was ready for this and she's doing this all on her own or if Dean was in on it too, but whatever it is, they're crossing a line that Sam never thought they'd cross, and neither of them have a problem with it.

Dean's biting his lip when Sam looks up at him. He shivers when Lisa kneels down behind him, breath catching in his chest when she circles his asshole with a slick finger.

"Ready for me, Sam?" she asks, breath hot against his shoulder.

"Yes, ma'am," he says, his mouth dry.

"Oh, I think you can do better than that," she says, tapping on his asshole.

Sam lets out a squeak, and for the first time in his life, his brother doesn't tease him about it.

"Are you ready for me, Sam?" she asks again, and Sam can hear the smirk in her voice.

Sam closes his eyes. "Please."

"Please what?" she asks.

Sam is just about to try for another 'please' when she reaches around and grabs his chin with her left hand, forcing his head back and to the side. Her lips brush against his left ear.

"I don't fuck just anybody," Lisa says, voice low. "If I'm going to fuck you with my big, fat cock, I want to know you really want it. So make it good or I'll fuck Dean instead while you're left just jerking off in the guest bedroom tonight to the sounds of your brother begging me to fuck him harder. Because Dean? He knows how to beg. He's good at it. And I give him exactly what he wants because he's a good boy for me. Are you gonna be a good boy for me?"

Sam wonders if he can die just from being so fucking turned on. His body is almost numb, his thighs shaking and he hasn't even done anything but kneel on the floor.

"Yes, ma'am. I'll be a good boy for you," he says, voice raspy. "Please. Please fuck me with your big cock. Please fill me up and fuck me until you're done with me. Please let me come. Let me come with your cock inside me. I'll be good for you. Just please let me come. Please fuck me."

"Fuck," Dean breathes.

Sam opens his eyes when she lets go of his chin, and he smiles when she licks the shell of his ear.

"That was hot," she says, then pushes two fingers into him.

Sam hisses, because he hasn't been fucked in a while, but it's good. It's so good. And she's rough with him, her fingers fucking him, the back of her hand hitting his ass as she moves in and out of his hole. She pushes a third finger in and presses down hard on his prostate.

"Oh, fuck!" Sam whimpers, falling forward, face just inches from Dean's hard cock, but he doesn't care because he's coming dry, his body shaking as his legs decide they don't need to hold him up anymore.

He's not even recovered when she shoves her cock into his still-spasming hole, and he cries out, back arching and nails digging into Dean's legs. Dean's eyes are wide, and he's still biting his lip, hand still as he sits there just holding his own dick, like he forgot what he was doing.

Lisa grabs his shoulders for leverage and starts pounding away in him. He regains the ability to use his legs and sits up again, leaving marks on Dean's legs but upright and holding still for her as Lisa fucks him so hard it's rocking Dean back and forth.

Dean's eyes are dark, and as Sam watches him, he realizes there's no going back. This thing they're doing. What they've done. It's not only fucking hot but it's opened up a new world to him, and Sam doesn't want to close the door on it. He doesn't know where it'll take them, but Sam wants to see that look in Dean's eyes over and over again.

Wants to pile in bed with the two of them. Wants to see Dean biting his lip. Wants to kiss Lisa, hold her, and see just why Dean comes back to her. Wants to watch as Lisa fucks Dean, her breasts bouncing as she makes Dean cry out and whimper and beg. Wants to lose himself in the both of them.

"You didn't ask permission," Lisa says.

Sam has no idea what she's talking about, but he sees the sheepish look on Dean's face.

"Can I come?" he asks.

"What do you think, Sam?" Lisa says, panting against his shoulder. "Should we let him come?"

"It's up to you, ma'am," Sam says.

"Mmm, such good boys," Lisa says as if she's groaning it out from somewhere deep inside, like it turns her on so much she almost comes just hearing him say it. "Come whenever you want, Dean."

"Yes, ma'am," Dean says, grinning because he knows she likes it.

Already stroking himself fast, a sound Sam knows well, knows Dean's close because they grew up with just a few feet separating them, because who has the time or patience for modesty when you figure out what your dick is for.

"Mmm, yeah," Dean moans, fucking up into his fist, way beyond any sort of finesse as he just gets there as quickly as he can, and when he comes, he looks Sam in the eye and winces, mouth open as he pants and moans, painting his own stomach with his release.

"Such good boys," Lisa says as she wraps her arms around him and grabs his cock with her right hand.

"Ah, fuck," Sam hisses, trying to hold it back.

He was already so close, and she's fucking him harder, rutting against him as if she's just using him to get off herself, and if it weren't for the reach-around, he'd think that's what she was doing, and he'd be totally fine with that because she's panting against his shoulder, her breasts plastered to his back, and her cock is filling him up, his asshole getting sore in just the right way.

"Oh, yeah, yeah," Lisa cries out, her forehead resting on his back, her hand tight around his cock, almost too tight, and she lets out one more whimper before she's coming. "Oh! Oh, fuck! Oh, fuck, Sam!"

Sam doesn't even try to stop himself. He comes, his cock jerking in her hand as he pushes back, meeting her thrusts. She slows down and finally stops, melting against his back and squeezing the last of Sam's release out of his cock.

"Can we do that again?" Dean asks.

Sam snorts as Lisa chuckles, shaking her head against Sam's back. She pulls out of him gently and stands up, reaching out to give Sam a hand. He takes her help, then the two of them get Dean up, and soon the three of them are piled on the bed, limbs everywhere.

And Sam feels right. It feels good. They fall asleep, Dean's cold feet pressing against his calves and Lisa's hair in his face.

He hopes Lisa's answer to Dean's question is yes.

**Part 4: Charlie**

Sam's face turns bright red. "I'm sorry! I'm so sorry!" he says, holding up his hands and backing out into the hallway. "I... I'm leaving! Sorry! I'm sorry!"

Charlie laughs as she continues fucking the girl she picked up the night before. "You might wanna close the door," she says, then winks at Sam.

Sam sputters out a few syllables, not even sure what he was trying to say, all he can see is Charlie. The straps tight across her body, her long legs. He wonders how big the attachment is on the harness, what it feels like. He just knows Charlie is good at using the thing. She has to be.

"Unless you wanna join in," Charlie says, smirking.

"Eww, no," the girl beneath her grumbles.

Sam had forgotten about her and startles, wide eyes locking with hers for a moment. "Sorry!" he says, fumbling to close the door and yelping when he stubs his own toe with the door.

Later that day Sam's hiding. He knows he's hiding. Charlie probably knows it. Dean doesn't know what happened, but he knows it's good, and he's been trying to get the truth out of Sam all day.

There's a knock on his bedroom door, making Sam flinch. He sits up straighter on the bed, heart rate picking up. "Yeah?"

Charlie opens the door and peeks in. "Are you over it yet?" she asks, grinning.

"Me? I'm fine," he lies, waving her off.

She walks in anyway, still grinning. "No, see, I know that look on your face. And it's not your 'I'm fine' face."

"I'm really sorry," Sam says, letting out a sigh. "I know I should've knocked, but I thought your girl was gone and we all barge in on each other. But I still should've knocked."

"I'm not upset, Sam," Charlie says, shaking her head.

"Oh, okay," Sam says, nodding. "T-that's good."

"Rachel wasn't up for a threesome with you," Charlie says, "but she wasn't upset either."

"Good," Sam says, forcing a smile. His neck feels hot, the tips of his ears, and he just knows he's blushing again.

"So?" Charlie drawls.

"Huh?"

"The offer's still out there," Charlie says, shrugging.

"What offer?" Sam asks, brow furrowing.

"You couldn't stop staring at my strap-on," she says, grinning.

Sam's eyes widen. "I didn't mean to... I-"

"Stop freaking out long enough to think about what I'm saying, Sam," Charlie says, chuckling.

Sam stares at her, and then it hits him. "Oh fuck," he breathes.

"Yeah," she says, nodding.

"Really?" he asks, sitting forward. "But I thought you were, you know. Girls?"

Charlie shrugs. "I like girls better, and fucking me isn't on the table. Fucking you? Hell yeah. Especially after I saw that look on your face."

"What do you mean?" he asks, trying for innocent, but failing miserably.

Charlie rolls her eyes. "You're cute when you think you're being all cool."

Sam freezes as her hands go to the front of her jeans. She unbuttons, unzips, and out pops the dildo attached to the harness.

"Wanna know what it's like to have my dick in your hole, Winchester?" she asks, wiggling her hips back and forth, making the dildo bounce.

Sam's cock was already half hard, but it decides it really likes Charlie's offer and things get tighter inside his jeans.

"You can say no if you want," Charlie says, then takes a few steps, close enough to the end of his bed that her knees rest against it. She strokes her cock. "Or you can come down here and suck me."

Sam winces, pressing down on his crotch, but then he's moving, crawling to the end of the bed before he really makes a conscious decision. He sits on his heels, looking up at her. "Yeah?" he asks.

Charlie reaches down and grabs the base of her cock, waving it back and forth. "Suck me."

It's awkward because she's not very tall. Sam stretches out on his stomach at the end of the bed and opens his mouth, groaning when she shoves her cock in.

"I hope you have lube in here," Charlie says. "I used the last of mine this morning."

Sam takes the cock all the way in, gagging a little, then pulls back. "Nightstand," he says, then sucks the cock down again.

She lets him suck for a moment, then pulls out and slaps his face with her cock. Sam groans, his own cock twitching

"Open your mouth and stick out your tongue," she says, and when he does, she slaps the cock down on his tongue a few times before sliding it over his lips, then smacks his cheek.

Sam's so turned on he's shaky. Charlie grins down at him, mischief in her eyes, and it makes Sam whimper.

"Bend over your desk," she says, nodding toward his desk.

"Fuck," Sam breathes as he climbs off the bed and gets into position. She hasn't told him to undress, so he just stands there, legs spread, ass pushed out a little, and his hands flat on his desk.

"Mmm, your ass is so cute," she says as she grabs his right ass cheek and squeezes.

Sam lets out a yelp as she smacks the other ass cheek with her opposite hand. His yelp ends on a groan, and he blushes when she chuckles.

"You like that?" she asks, clearly amused.

"Yes," he says, pushing his ass out more.

He shivers as she reaches around and opens up his jeans. She hooks her fingers under his jeans and boxers, then slowly pulls them down over the curve of his ass, down his long legs, and lets them pool at his ankles.

Sam flinches and squeaks when she smacks his right ass cheek. She's stronger than she looks, and it really stings, but it feels good, and he wants more.

"You liked that," she says as she traces the sore spot on his ass with a finger. By the tone of her voice, she's getting a kick out of his reaction.

Sam chuckles, then hisses as she smacks the other ass cheek. She traces that sore spot too, then she's gone. He looks over his shoulder and sees her heading for his bedside table. She opens the drawer and pulls out his lube, opens the top, and looks up at him, smirking.

"You want this so much you're biting your lip," she says as she walks up to him and rests her left hand on his ass.

Sam nods, not really having realized he was biting his lip, but he really does want it, wants her.

"My cock isn't that big," she says. "You game for just taking it? No prep?"

Sam shivers again. "Yes," he hisses.

Charlie smiles. "Okay, then put your chest down on the desk and spread your knees so I can reach you."

"Yes, ma'am," Sam says as he lowers himself. She's still fully clothed other than the cock bouncing between the V of her jeans. It makes him feel even more naked, the boxers and jeans around his ankles somehow doing the same thing.

He rests his right cheek on the desk and grabs the far edge of the desk with both hands, spreading his knees as she slicks up her cock. Soon it's nudging at his hole. He closes his eyes and relaxes as much as he can, tilting his hips. She moans as she grabs his ass cheeks and spreads them wide, the tip of her cock sliding into his hole.

Someone who's never taken a cock up their ass would be having a hard time with it, but the cock is small enough that Sam just feels a slight burn, but mostly it feels amazing. She starts fucking him, and just as he's thrusting back, trying to meet her and get more stimulation, she reaches up and tickles his ribs on both sides.

"Hey!" he says, wriggling around. He's smiling, because it's adorable and cute, especially when she giggles.

"Is everything ticklish?" she asks, and damn she sounds mischievous.

"No," Sam says, then chuckles as she reaches around him and tickles his belly.

"Hmm, that's ticklish," she says.

He holds his breath as her fingers trail downward. He's expecting her to play with his cock or balls, so when she digs in at the crease between his leg and pubic area, he lets out a loud bark of laughter, twisting to the side, chest lifting off the desk. She giggles again, but then her right hand wraps around his cock and she starts stroking, not so much fucking him as just grinding.

Sam smiles as she kisses his back, her left hand smoothing over his left flank, and he chuckles as she blows a raspberry on his back. Her hands are everywhere, it seems, and he gets lost for a while, just a drifting as she pinches here, tickles there, kisses up and over, caresses this, and rubs her cheek and nose over that.

"Okay, you're a big guy, and I'm having trouble fucking you as hard as I want to," she says as she smacks his right ass cheek and pulls out.

He's up for whatever she wants. "Just tell me what to do," he says.

"Leave the clothes here and get on the bed so I can have my wicked way with you," she says.

He turns around and almost chokes. She's standing there stroking her cock, like it's real, like she wants to keep it hard while she waits for him. She's doing it in such a casual way, as if she's not even thinking about it, and Sam's dick twitches just watching her.

"Well?" she prods, smirking.

"Sorry," he says, blushing. He steps out of the boxers and jeans, then lifts one leg at a time and pulls each of his socks off before hopping onto the bed and spreading out. He looks back up at her and smiles. "Is this where you want me?"

"Right like that," she says as she gets onto the bed and straddles the backs of his legs.

He gasps as she shoves her cock back into him, and yeah, it feels much better this way. She pokes his right side with her finger, making him chuckle and flinch.

"That's totally adorable," she says, and he can hear her grinning just by the way she says it. "And really fuckin' hot."

Sam pushes back to meet her thrusts even though he's really not moving all that much. Her cock isn't as big as he's used to when it comes to harnesses, but it does have a ridged head, and if she were to just change her angle a little bit, he thinks he could get off without ever touching his cock. He whines as he tries to change the angle, wriggling around in the hopes he can get there.

"Can you come like this?" she asks, and she's moving, trying out different angles and ways of thrusting into him.

"Fuck yeah," he says, his body jerking. "Yeah, right there! Right there! Harder! Oh, fuck, yeah!"

"Oh! Oh, fuck! You like it _that_ much?" she asks, her movements becoming uncoordinated, her voice getting breathier and really fucking hot. "I figured you really liked this, but I didn't know you could get off like this! That's so f-yeah! Oh, fuck, yes! I want you to c-oh, fuck. Oh, f-fuck! I want you to come like this. Just like this!"

She's already coming, fucking down into him and possibly leaving bruises on his sides where her fingers are digging in, holding him tightly. She leans down and bites his back, and that's it. Sam's coming on his sheets, moaning and thrusting back as she grinds down.

"Mmmh, fuck yeah, that was hot," she slurs, her lips tickling his back. She climbs off him and smacks his ass. "That was fuckin' hot, dude!" 

Sam smiles as he pushes himself to his hands and knees. "Payback time!" he says as he straddles her thighs.

"Ah! No!" she squeals as he tickles her sides and tummy. She twists and smacks at his upper arms, laughing with her eyes squeezed shut.

He leans down and blows a raspberry on her neck just under her right ear, making her laugh even harder. She pinches one of his nipples and he lets out a yelp, falling off her and sprawling out on the bed next to her. 

She turns and throws her left leg over him and uses his left arm as a pillow, snuggling up next to him.

Charlie runs her fingers over his chest. "So how long are we gonna make Dean wait before giving him details?"

Sam chuckles. "A long time. Really make him beg."

"Okay, and when you do tell him, let me know," Charlie says. "Then ask him if he wants to watch me fuck you."

Sam lets out a bark of laughter as he pulls her on top of him and tickles her sides, laughing harder as she giggles and squirms.

**Part 5: Dean**

"Order another movie," Sam says as Dean flops around on the bed again, sighing dramatically. They're stuck in some random motel in some random town, snowed in and bored.

"Too expensive," Dean grumbles into the sheets. He's face-down on the bed, right foot hanging off the far side of the bed, left arm dangling off the side of the bed closest to Sam.

Sam snorts. "Jerry Dixon is paying for the room. He doesn't care if you order another movie."

"Boring," Dean sing-songs.

Sam rolls his eyes. "Fine. I'll just sit here and amuse myself," he says, then pulls his cock out through the slit in his boxers.

Dean does a double-take. And then he stares. They don't do this all that often. After Lisa, it was a painful reminder they'd never be normal, which was ironic in and of itself, but normal is overrated anyway. So they didn't share women after her, and they went back to that closer-than-normal-siblings thing they had going where they'd jerk off in the same room or bring a woman back for a night, but they mostly kept to themselves.

"Told you to get laid," Dean mumbles.

Sam chuckles. Because yeah, Dean did tell him just days before the storm hit that Sam needed to get laid. Sam strokes himself slowly, not in a hurry to come.

"It's been a while," Sam says casually.

"How long?" Dean asks, wriggling around on the bed until he's got his right arm underneath himself. He probably doesn't care if Sam knows what he's doing.

"Five months," Sam says.

"Dude, five months since you got laid?!" Dean says, getting to his knees, eyes wide. And yeah, he's got his right hand down his boxer briefs.

"No, five months since Charlie fucked me," Sam says. He actually got laid just two weeks ago, but he wants to tease, and Charlie's the last woman that fucked him in the ass.

"Oh, fuck," Dean breathes, wincing as he bends at the waist. "You didn't tell me she fucked you. Asshole," he complains. "Details! I want details!"

"I can't," Sam says. "She said she didn't want anyone to know."

"No, she didn't," Dean says, smirking. "I know Charlie better than that."

Sam chuckles. "You're right. She said to save it for a special occasion."

"That's more like it," Dean says, shoving his boxer briefs down until the elastic band catches under his balls. "Now spill."

"Is this a special occasion?" Sam asks. "Because it kinda just seems like we're bored and horny. Nothin' special about it," he says as he waves his cock around.

Dean sighs. "Dude, you know I'm really bad at giving blowjobs, so think of something else."

Sam snorts. Yeah, Dean's terrible at it. Which Sam finds hilarious because the first thing people assume when they see Dean's lips is that they'd look great wrapped around a cock. And while they definitely do look good, all plump and spit-slicked stretched around a cock, it's not worth the awful blowjob.

Or the scrapes whenever Dean forgets to cover his teeth. Or the bitching a guy has to put up with because Dean can't control his gag reflex and his mouth tastes like bile for the rest of the day.

"I'm thinkin' it's been a long time since I got fucked," Sam says as he hooks his thumbs under the elastic of his boxers and slides them off. "Got lube?"

"Fuck, yeah," Dean says, almost face-planting on Sam's bed because he gets up too fast and his boxer briefs tangle around his ankles. But then he's back with the lube from his duffel.

Sam takes the tube and grins up at Dean. "Wanna watch?" he asks.

"Nah, I think I'm gonna get that pay-per-view," Dean says, rolling his eyes.

Sam flops down onto his stomach, cross-wise on the bed, and spreads his legs, his lower legs dangling off the bed. He opens the tube and squirts some of the lube onto his fingers before reaching back and circling his hole.

"Lookin' a little tight there, Sammy," Dean says.

It boggles Sam's mind how Dean can make him blush even after all these years. Dean has seen everything, touched everything, and yet dirty talk out of Dean's mouth can make Sam blush so hard his ears get hot.

"I walked in on Charlie with that chick she was bangin' for a while," Sam says, changing the subject.

"Seriously?!" Dean says. "Damn it, why do you get all the fun?!"

Sam chuckles. "It wasn't fun at the time. I felt really bad. The chick was grossed out and I hid in my room for a while."

"Jerkin' off?" Dean asks, and Sam can hear the grin.

"No. I just stayed hard until she showed up in my room and pulled out her cock," Sam says.

The noise that comes from Dean makes Sam's cock twitch. It's a deep groan followed by a whimper, and Sam knows Dean's got his own cock in hand, stroking.

"She made me suck it," Sam says as he pushes two lubed fingers into his hole. He spread his legs wider and arches his back, showing off for Dean. "Then she fucked me over my own desk."

"Ah, shit, Sam," Dean gasps.

Sam laughs as Dean stumbles into him and pushes his hand away from his ass, and he squirms on the bed as Dean pushes three fingers into him, pumping in and out.

"She's fuckin' adorable," Sam says. "Really playful during sex. She tickled me and smacked my ass while she fucked me."

"Was she good at it?" Dean asks, pulling his fingers out and slapping his cock down on Sam's wet hole.

"Hell, yeah," Sam says. "She's really flexible, and-oh, fuck."

Dean shoves his cock into Sam's hole and goes balls deep in one long thrust. "What was that, Sammy?" he asks, cocky and confident.

"She did somethin' I've never had any chick do before," Sam says.

Dean isn't rough like the women Sam usually chooses. He'll pretend, and even shove Sam around a little because he knows Sam likes it rough, but then he'll fuck Sam like he's caressing him from the inside out and tending to all of Sam's senses, not just getting both of them off. Sam loves it.

"Yeah? What's that?" Dean asks.

Sam moans as Dean reaches around and grabs his cock. Sam's flat on the bed, so Dean doesn't really have room to do much, but the rhythmic squeezing is more than enough to get him there.

"She blew a raspberry on my back while she was fucking me," Sam says, pushing back to meet Dean's thrusts.

"She's fuckin' adorable," Dean breathes before placing a kiss on Sam's back. "Was it hot? Or was it just cute?"

"She had already been fucking me for a while," Sam says, "and when she did that and then bit me it just kinda blew my mind, and I came all over the bed."

Dean chuckles, low and dirty in his ear. "Think she'd do it again and let me watch?"

Sam groans as the scene plays out in his head. "I'll ask."

"Really?" Dean asks as he fucks Sam a little faster. "You don't think the whole brothers thing would freak her out?"

"Dude, did you not notice the twins she hooked up with?" Sam asks, squeezing his eyes shut as Dean starts fucking him just right, Dean's hand on his cock almost enough to push him over the edge. "The ones you drooled over and propositioned at the bar?"

"Oh, fuck, I thought they were just friends," Dean hisses, his movements on Sam becoming uncoordinated as he just ruts into him.

Sam groans, squirming beneath Dean as he gets closer. He sucks in a quick breath as Dean starts rubbing just under the head of his cock, that small bundle of nerves that drives Sam crazy.

"No, not friends," Sam says, panting. "Friends don't spitroast other friends with their harnesses."

"Fuck, Sa-Sam! Shit, oh shit," Dean hisses, fucking Sam hard as he comes deep inside him.

Sam would laugh at him if it wasn't for the fact that he's so close to coming that he's ready to beg, but Dean, the asshole, slows down, his hips not even moving anymore.

"Dude! I wanna come!" Sam growls, wiggling around.

Dean chuckles. "Aww, you didn't get to come?"

Sam reaches back with both hands and pinches at Dean's sides. It's awkward, but years of wrestling with Dean means he's perfected moves like this.

"Hey!" Dean yelps as he squirms on Sam's back. "I was just teasing! I'll get you off!"

"Well, come on!" Sam says, trying to buck Dean off.

"Knock it off or I'll blow you," Dean says, laughing.

Sam pinches him more. "You do that and I'll kick your ass."

"Okay! Okay!" Dean says, climbing off Sam and turning him over. "Ya big baby," he says as he straddles Sam's right leg and grabs his cock, stroking fast and just the way Sam likes it.

"Mmm, yeah, like that," Sam says, hands fisting the sheets at either side of him.

Dean rolls his balls with his free hand, then gives them a tug at just the right moment, and Sam's gone, coming so hard he arches his back and makes a mess of his own stomach and Dean's hand. Sam lets out a sigh of contentment as Dean flops down on the bed next to him.

"Well, fun as that was," Dean says, "I'm bored again."

Sam's had enough, so he climbs on top of Dean and tickles him until Dean tugs him off by his hair, both of them laughing and falling off the bed.


End file.
